2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro PGF1 compounds

ABSTRACT

This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.

The present application is a continuation application of Ser. No. 778,649, filed Mar. 17, 1977; which is a divisional application of Ser. No. 647,363, filed Jan. 8, 1976, now U.S. Pat. No. 4,028,419.

The present invention relates to prostaglandin analogs, for which the essential material constituting disclosure therefor is incorporated by reference here from U.S. Pat. No. 4,028,419. 

I claim:
 1. A prostaglandin analog of the formula ##STR1## wherein Y is trans -CH=CH-; wherein M₁ is ##STR2## wherein R₅ is hydrogen or methyl; wherein L₁ is ##STR3## or a mixture of ##STR4## wherein R₃ and R₄ are hydrogen, methyl, or fluoro, the same or different, with the proviso that one of R₃ and R₄ is methyl only when the other is hydrogen or methyl;wherein g is one, 2, or 3; and wherein m is one to 5, inclusive.
 2. A compound according to claim 1 wherein m is one or
 2. 3. A compound according to claim 1, wherein m is 4 or
 5. 4. A compound according to claim 1, wherein m is
 3. 5. A compound according to claim 4, wherein g is one.
 6. A compound according to claim 5, wherein at least one of R₃ and R₄ is fluoro.
 7. A compound according to claim 6, wherein R₃ and R₄ are both fluoro.
 8. A compound according to claim 7, wherein R₅ is hydrogen.
 9. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-16,16-difluoro-PGF₁α, a compound according to claim
 8. 10. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-16,16-difluoro-15-epi-PGF₁α, a compound according to claim
 8. 11. A compound according to claim 5, wherein at least one of R₃ and R₄ is methyl.
 12. A compound according to claim 11, wherein R₃ and R₄ are both methyl.
 13. A compound according to claim 12, wherein R₅ is hydrogen.
 14. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-16,16-dimethyl-PGF₁α, a compound according to claim
 13. 15. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-16,16-dimethyl-15-epi-PGF₁α, a compound according to claim
 13. 16. A compound according to claim 5, wherein R₃ and R₄ are both hydrogen.
 17. A compound according to claim 16, wherein R₅ is methyl.
 18. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-15-methyl-PGF.sub.1α, a compound according to claim
 17. 19. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-15-epi-15-methyl-PGF₁α, a compound according to claim
 17. 20. A compound according to claim 16, wherein R₅ is hydrogen.
 21. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-PGF₁α, a compound according to claim
 20. 22. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-15-epi-PGF₁α, a compound according to claim
 20. 